Beyond the Listings: A Glimpse into Debra’s World

An interviewer recently asked me about my life beyond real estate and requested a one-sentence reply. How amusing. I could write a book filled with cherished memories, but for now, let’s start with this:

I was born in South Deering and raised by my loving parents alongside my three brothers—Michael, and the twins, Dave and Steve. I’m the eldest sibling, and my Italian grandparents were also a significant part of our lives. During high school, I stood out as a star baseball pitcher. As a youngster, you could find me on the playground selling candy to fund my latest obsession of that moment. My brothers, who are near and dear to me, often say that I’ve been the problem-solving, bossy one since the age of five. As a teenager, I took charge whenever and wherever I could, and I had a knack for empathizing with others and helping to solve their problems. Despite having a supportive and loving family, I felt an unyielding curiosity to see the world and do something different from what I had known growing up. I accelerated my education, completing my junior and senior years in one, and moved to Lake Tahoe, Nevada.

Upon returning to Chicago, I embarked on a career in marketing, produced a play, and even opened the city’s first Gelateria after receiving training in Italy. When my business partner moved to California and my landlord rejected my personal guarantee on our lease, I had to sell the business. One of my regular customers, a real estate developer, advised me to ‘take a week to have a pity party and then get your real estate license to come and join my team.’ So I joined his ‘sales team’ (which turned out to be just him and me), and together, we sold the first loft condo conversion in Chicago at 411 S Sangamon and 913 W Van Buren.

That marked the beginning of my 39-year career in real estate. Today, half of my team consists of family members, including two of my brothers and my daughter Katharine, and the other half consists of like-minded individuals who I adore.

Katharine and I love hosting Sunday Suppers, sometimes a simple supper and often a grand affair Italian style, with anywhere from 6 to 26 guests – family, friends and clients. My daughter is an excellent chef and I excel at setting a pretty table and cleaning the very messy kitchen; we make a good team. When we can take a day or better yet, the weekend, our happy place is snuggled on the sofa with our doggies binge watching we Law & Order SVU, Austin Powers, James Bond, and Lord of the Rings.

In my leisure time, I enjoy mixing margaritas under my own label, Wacky Girl Margaritas. I also love cooking, traveling, and whacking balls at the driving range. I’m currently working on a board/card game in collaboration with my daughter and close family friends. While people often perceive me as serious…I do love to geek out over a spreadsheet, I have a playful wacky side a la Lucille Ball. Just watch the video of me jumping into a pool fully clothed!.

I’m fortunate to live in Lincoln Park for the past 20 years, where I can walk to my favorite local businesses and engage with my community. We all know each other by name, even our dogs. Speaking of which, I have three—Winston, Tapper, and Stella—each with their own unique rescue story.

I find joy in exploring Chicago’s vibrant culture and most of all, its people. Work allows me the privilege of constant change, meeting incredible individuals who often become friends. As I approach my 40th year in real estate, I feel truly blessed that my personal and professional lives have intertwined so seamlessly.